Electrochemically Enabled C-Terminal Peptide Modifications
© 2021. The Author(s), under exclusive license to Springer Science+Business Media, LLC, part of Springer Nature..
Modified peptides serve as promising therapeutic leads, valuable tools for chemical biology, and diverse functional materials. Synthetic strategies which enable the direct modification of native peptide sequences are particularly attractive for the rapid generation of designer peptides. This chapter details an operationally simple electrochemical approach to the modification of the peptide C-terminus, which proceeds via direct anodic oxidation of C-terminal peptide carboxylic acids. Electrochemical decarboxylation affords a key N,O-acetal intermediate, which can be engaged with various nucleophiles. Herein, step-by-step protocols for C-terminal arylation and sulfonylation are presented to highlight the utility of the method for the preparation of valuable functionalized peptides.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:2355 |
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| Enthalten in: |
Methods in molecular biology (Clifton, N.J.) - 2355(2021) vom: 12., Seite 131-139 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Lin, Yutong [VerfasserIn] |
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| Links: |
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| Themen: |
Anodic oxidation |
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| Anmerkungen: |
Date Completed 11.01.2022 Date Revised 11.01.2022 published: Print Citation Status MEDLINE |
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| doi: |
10.1007/978-1-0716-1617-8_12 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| 520 | |a Modified peptides serve as promising therapeutic leads, valuable tools for chemical biology, and diverse functional materials. Synthetic strategies which enable the direct modification of native peptide sequences are particularly attractive for the rapid generation of designer peptides. This chapter details an operationally simple electrochemical approach to the modification of the peptide C-terminus, which proceeds via direct anodic oxidation of C-terminal peptide carboxylic acids. Electrochemical decarboxylation affords a key N,O-acetal intermediate, which can be engaged with various nucleophiles. Herein, step-by-step protocols for C-terminal arylation and sulfonylation are presented to highlight the utility of the method for the preparation of valuable functionalized peptides | ||
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